Diprenylated phenolic enantiomers from Artemisia scoparia

Investigation on the chemical constituents of Artemisia scoparia resulted in the isolation of sixteen compounds, including undescribed six pairs of diprenylated phenolic enantiomers (±)-scopacoumaricin A-F, and two pairs of cis-trans isomers cis/trans-scopacoumaricin G and cis/trans-artepillin A. Trans-artepillin A was obtained from this plant for the first time. The structures of the isolates were proposed by analysis of their 1D, 2D-NMR and HRESIMS spectroscopic data. Their absolute configurations were determined by comparison of their experimental and calculated electronic circular dichroism spectra. Evaluations of the anti-inflammatory activity revealed that (−)-scopacoumaricin D, (+)-scopacoumaricin F and cis-scopacoumaricin G showed moderate anti-inflammatory activity on lipopolysaccharide-induced nitric oxide production in RAW264.7 cell.